Isopropanol → HCID 14770070, compound

HRID 1087527Notes

Reaction equation

HRID 1087527 reaction equation
C(N(CCCC)CCCC)CCC.[CH:14]([OH:17])([CH3:16])[CH3:15].[O:18]=[C:19]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][C:26]([C:35](O)=[O:36])=[C:25]2[N:20]1[CH2:21][CH2:22][C:23]1[CH:40]=[CH:39][S:38][C:24]=12.[I-].C[N+]1C=CC=CC=1Cl>C(Cl)Cl>[O:18]=[C:19]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][C:26]([C:35]([O:17][CH:14]([CH3:16])[CH3:15])=[O:36])=[C:25]2[N:20]1[CH2:21][CH2:22][C:23]1[CH:40]=[CH:39][S:38][C:24]=12

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 14666689HCID 14666689, compound

Product 1

HCID 14770070HCID 14770070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.1 ml of tri-n-butylamine and 6.1 ml of isopropanol were added to a suspension of 2.0 g of 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2.3-a]quinolizine-10-carboxylic acid and 3.8 g of N-methyl-2-chloropyridinium iodide in 12.5 ml of methylene chloride, the reaction mixture was stirred under reflux for 24 hours, evaporated in vacuo and the residue was chromatographed on silica gel with toluene/ethyl acetate (9:1). After crystallization from methanol, there was obtained pure isopropyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate of m.p. 165.5°-166°.

Workup

  1. temperatureunder reflux for 24 hours
  2. customevaporated in vacuo
  3. customthe residue was chromatographed on silica gel with toluene/ethyl acetate (9:1)
  4. customAfter crystallization from methanol

Sources & evidence

ORD record
ord-2988bb1435c444c38aa7851a46ace019
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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